Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines

doi:10.6023/cjoc201708028

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (3): 642-647.DOI: 10.6023/cjoc201708028 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

Articles

手性脲衍生物有机催化α-萘酚和N-Ts芳香醛亚胺的不对称aza-Friedel-Crafts反应

王黎明, 林赓, 赵美君, 刘东垚, 金瑛

吉林医药学院药学院吉林 132013

收稿日期:2017-08-15 修回日期:2017-10-15 发布日期:2017-11-17
通讯作者: 金瑛,E-mail:jinying2288@163.com E-mail:jinying2288@163.com
基金资助:
国家自然科学基金（No.21102055）、吉林省教育厅（No.JJKH20170409KJ）及国家级大学生创新创业训练计划（No.201713743010）资助项目.

Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines

Wang Liming, Lin Geng, Zhao Meijun, Liu Dongyao, Jin Ying

Department of Pharmacy, Jilin Medical University, Jilin 132013

Received:2017-08-15 Revised:2017-10-15 Published:2017-11-17
Contact: 10.6023/cjoc201708028 E-mail:jinying2288@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21102055), the Department of Education of Jilin Province (No. JJKH20170409KJ) and the National Students' Program for Innovation and Entrepreneurship Training (No. 201713743010).

1. Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines.PDF(1472KB)

Abstract

Chiral urea derivatives as organocatalysts were applied in the asymmetric aza-Friedel-Crafts reaction of α-naphthol with 14 N-tosyl aldimines. The desired chiral aminoarylnaphthols were obtained in 70%~86% yields with up to 78% enantiomeric excess (ee) under the screened optimal condition. The catalyst type and the substrate scope were broadened in this methodology.

Key words: chiral urea derivatives, asymmetric catalysis, α-naphthol, aza-Friedel-Crafts reaction

Cite this article

Wang Liming, Lin Geng, Zhao Meijun, Liu Dongyao, Jin Ying. Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines[J]. Chin. J. Org. Chem., 2018, 38(3): 642-647.

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[1] (a) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem., Int. Ed. 2004, 43, 550.
(b) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
(c) Nicolaou, K. C.; Reingruber, R.; Sarlah, D.; Bräse, S. J. Am. Chem. Soc. 2009, 131, 2086.
(d) You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190.
(e) Ling, J.; Lam, S. K.; Lo, B.; Lam, S.; Wong, W.-T.; Sun, J.; Chen, G.; Chiu, P. Org. Chem. Front. 2016, 4, 457.
(f) Li, J. J.; Tan, C. H.; Mu, X. P.; Gong, J. X.; Yang, Z. Chin. J. Chem. 2017, 35, 562.
[2] (a) Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
(b) Wang, Y.-Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
(c) Niu, L.-F.; Xin, Y.-C.; Wang, R.-L.; Jiang, F.; Xu, P.-F.; Hui, X.-P. Synlett 2010, 765.
(d) Wang, S.-G.; You, S.-L. Angew. Chem., Int. Ed. 2014, 53, 2194.
(e) Zhou, D.; Huang, Z.; Yu, X. T.; Wang, Y. X.; Li, J.; Wang, W.; Xie, H. X. Org. Lett. 2015, 17, 5554.
(f) Wang, Y. C.; Jiang, L.; Li, L.; Dai, J.; Xiong, D.; Shao, Z. H. Angew. Chem., Int. Ed. 2016, 55, 15142.
[3] (a) Bandini, M.; Melloni, A.; Tommasi, S.; Umani-Ronchi, A. Synlett 2005, 1199.
(b) Wang, Y. Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
(c) Kang, Q.; Zhao, Z.-A.; You, S. L. J. Am. Chem. Soc. 2007, 129, 1484.
(d) Terada, M.; Yokoyama, S.; Sorimachi, K.; Uraguchi, D. Adv. Synth. Catal. 2007, 349, 1863.
(e) Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608.
(f) Qian, Y.; Ma, G. Y.; Lv, A. F.; Zhu, H.-L.; Zhao, J.; Rawal, V. H. Chem. Commun. 2010, 46, 3004.
(g) Xu, F. X.; Huang, D.; Han, C.; Shen, W.; Lin, X. F.; Wang, Y. G. J. Org. Chem. 2010, 75, 8677.
(h) Chen, L.-Y.; He, H.; Chan, W.-H.; Lee, A. W. M. J. Org. Chem. 2011, 76, 7141.
(i) Wang, X.-W.; Hua, Y.-Z.; Wang, M.-C. J. Org. Chem. 2016, 81, 9227.
(j) Liu, H.-H.; Zhang, D.-H.; Wang, X.-H.; Meng, W.-D.; Huang, Y.-G. Chin. J. Org. Chem. 2016, 36, 1351(in Chinese). (刘海华, 张东华, 王夏辉, 孟卫东, 黄焰根, 有机化学, 2016, 36, 1351.)
[4] (a) Trost, B. M.; Müller, C. J. Am. Chem. Soc. 2008, 130, 2438.
(b) Sheng, Y.-F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899.
(c)Wang, W. T.; Liu, X. H.; Cao, W. D.; Wang, J.; Lin, L. L.; Feng, X. M. Chem.-Eur. J. 2010, 16,1664.
(d) Arai, T.; Awata, A.; Wasai, M.; Yokoyama, N.; Masu, H. J. Org. Chem. 2011, 76, 5450.
[5] (a) Enders, D.; Seppelt, M.; Beck, T. Adv. Synth. Catal. 2010, 352, 1413.
(b) Bai, S.; Liao, Y. T.; Lin, L. L.; Luo, W. W.; Liu, X. H.; Feng, X. M. J. Org. Chem. 2014, 79, 10662.
(c) Montesinos-Magraner, M.; Vila, C.; Cantón, R.; Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R. Angew. Chem., Int. Ed. 2015, 54, 6320.
(d) Vukovic, V. D.; Richmond, E.; Wolf, E.; Moran, J. Angew. Chem., Int. Ed. 2017, 56, 3085.
[6] (a) Kocovsky, P.; Vyskocil, S.; Smrcina, M. Chem. Rev. 2003, 103, 3213.
(b) Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 2858.
(c) Brandes, S.; Bella, M.; Kjærsgaard, A.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 1147.
(d) Liu, T. Y.; Cui, H. L.; Chai, Q.; Long, J.; Li, B.-J.; Wu, Y.; Ding, L.-S.; Chen, Y.-C. Chem. Commun. 2007, 2228.
(e) Hong, L.; Wang, L.; Sun, W. S.; Wong, K.; Wang, R. J. Org. Chem. 2009, 74, 6881.
(f) Rueping, M.; Nachtsheim, B. J. Beilstein J. Org. Chem. 2010, 6, 1007.
(g) Takizawa, S.; Arteaga, F. A.; Yoshida,Y.; Kodera, J.; Nagata, Y.; Sasai, H. Dalton Trans. 2013, 42, 11787.
(h) Takizawa, S.; Hirata, S.; Murai, K.; Fujioka, H.; Sasai, H. Org. Biomol. Chem. 2014, 12, 5827.
(i) Montesinos-Magraner, M.; Vila, C.; Cantón, R.; Blay, G.; Fernández, I.; Muñoz, M. C.; Pedro, J. R. Angew. Chem., Int. Ed. 2015, 54, 6320.
[7] (a) Liu, G. X.; Zhang, S. L.; Li, H.; Zhang, T. Z.; Wang, W. Org. Lett. 2011, 13, 828.
(b) Chauhan, P.; Chimni, S. S. Eur. J. Org. Chem. 2011, 1636.
[8] Kumari, P.; Jakhar, A.; Khan, N. H.; Tak, R.; Kureshy, R. I.; Abdi, S. H. R.; Bajaj, H. C. Catal. Commun. 2015, 69, 138.
[9] Li, Y. W.; Wang, L. M.; Jin, Y.; Chang, S. Chirality 2017, 29, 458.
[10] (a) Cheng, L.; Liu, L.; Jia, H.; Wang, D.; Chen, Y. J.; Liu, L. J. Org. Chem. 2009, 74, 4650.
(b) Zhang, T. Y.; He, W.; Zhao, X. Y.; Jin, Y. Tetrahedron 2013, 69, 7416.

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手性脲衍生物有机催化α-萘酚和N-Ts芳香醛亚胺的不对称aza-Friedel-Crafts反应

Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines

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